High Bid

Story Info
I won the auction, now...
2.1k words
3.95
32.1k
4
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

It took a few weeks to work out the details but finally we got to meet in person. The hotel seemed nice with a large lobby opening onto an atrium where fountains and numerous plants gave the place an exotic feel. We had discussed possibly meeting for dinner or drinks but she said she didn't drink and that she thought she'd be a bit too nervous to eat much of anything.

I must admit I was feeling a bit nervous myself. We had only exchanged email and outside of a couple of pictures of my face she had no idea what I looked like. Of course I had the photos from the bid page and as long as they were actually of her I was okay. What made me a bit nervous is how she would react to my size. I wasn't morbidly obese but since I hit fifty I'd put on a fair amount of weight.

When I saw her walk past the check in desk head out for the lobby I stood up and waved, watching her face to see if I could see any surprise or disappointment. Her smile seemed genuine and I didn't notice any apprehension as I walked toward her, reached out my hand and said, "Christine, hi, I'm Michael. It's so nice to finally meet you."

"Yes, it's been a bit strange," she said as she took my hand and shook it.

"How was your flight?"I asked looking at the way her hair cascaded over her shoulders. The tight, dark curls stood out in contrast against her light yellow

"A bit bumpy," she replied, "but the limo ride was very comfortable. Thank you."

"Would you like to get some coffee or a bite to eat?"

"No, I had a soda in the limo and I'm a bit nervous to eat anything."

"I understand. Then would you like to head up," I said, nodding to the elevator.

She nodded, smiling then looking down as she lightly bit her lip. I stepped back and as she moved toward the elevator, I touched my hand to her waist and followed her in. Sliding my hand down to her hip, I could feel she was thin, not overly curvy.

"What made you decide to do this Christine?" I asked as I pressed the button and watched the door close.

"After reading online about the woman who..."

"And man."

"...the woman and man who auctioned their virginity I thought that I might could pay off some student loans."

"Were you disappointed?"

"Disappointed?"

"I mean my bid was a far cry from what... three quarters of a million."

"Well, she was very beautiful and I...," she paused, then shook her head.

"But you are beautiful. Mind you I am glad the price didn't go any higher because I couldn't have come up with a lot more cash now. It's in escrow now, just like we agreed."

She nodded, "Yes, thank you."

"This is our floor, room 908."

We headed down the corridor and into the room where she set her bag on the bed and asked, "If you don't mind," nodding to the bathroom.

I stepped back and watched her step into the bathroom and close the door. Turning on the lights and quickly undressing, I pulled on the terrycloth bathrobe and waited. As the bathroom door opened she immediately turned facing the mirror holding her hands in front of her breasts.

She still had on her panties but otherwise was naked. I got up from the bed and stepped up behind her, reaching out and touching both her shoulders with my hands.

"I'm sorry, I just..."

"No, no it's okay," I said, moving closer, feeling my cock slide over the satin fabric of the panties. Moving my hands down to hers, I moved them away from her breasts. They were small with perky, firm nipples. "Your nipples..."

"It's a little cold," she replied.

I pulled her closer to me, moving my hands up to her breasts as I pressed my cock against her. Kissing her neck I gently squeezed her breasts and then slid one hand down her stomach. Easing my fingers under the elastic waistband I slipped them through the soft, curly hair downward. Searching for her clit my fingers found a slight hollow and then, instead of the tiny nub I felt an all too familiar firmness.

"What the..." I said, stepping back.

"I, I can..."

"You're a man,"

"No, no you felt my breasts. I'm..."

"Show me. Take off your panties," I moaned, falling back onto the bed.

She eased her panties out over her erection and let them drop to the floor. Stepping forward I stared at her softening cock.

"You lied."

"No, I am a virgin. No man... no one has touched me."

"But the ad..."

"Read it, I never said I was... that I was pre-op."

"But you're not a woman."

"Not yet. And in the ad I only said I was a virgin, I didn't say..."

"The pictures."

"You recognized me, even called me beautiful."

Pulling my eyes away from her cock and looking up at her face and then her breasts I had to agree, man or woman, she was beautiful, a bit thin but beautiful.

"No one has touched you?"

"No."

"But what do I do?"

"Whatever you want," she replied.

"From behind?"

"I brought lubricant, it's in my purse."

"I've never..."

"Neither have I. My friends have told me a few things."

"Get the lube," I said, wondering if I had gone completely crazy. Standing up I dropped the robe and walked over to her. Reaching out I moved on arm around her and then held her breast with my other hand. Squeezing I said, "Okay, put the lube on."

Jumping slightly at the cold sensation of the lube I guided her hand over me, working it over the length of me. Feeling her trembling slightly I whispered, "Yes, that is good, now lick and suck on my nipples."

Still working her hand up and down my cock she stood up and moved her mouth to my chest. Her soft lips then closed over a nipple and she sucked. I could feel the tingling down to my cock. Losing myself to the sensation, I lowered my hand from her breast down her stomach, over the soft hair onto her cock.

It had already hardened some but as my fingers wrapped around it I could feel it firm up more. I had a sudden urge and stepped back a bit and then knelt down. Without thinking any more I slipped my mouth over her cock and began sucking. From the tip I tasted a sharp, bitter flavor that quickly subsided as I continued. Grasping her ass with both hands I tried to take as much of her into my mouth as I could. Even though her cock was rather small, I gagged on it as the head reached the back of my throat.

Backing away, I let her cock slip out of my mouth as I stood up. Pulling her toward me I wrapped my arms around her and kissed her on the lips, my tongue sliding into her mouth. It felt odd feeling our cocks pressing against each other. As we finished the kiss I moved her back onto the bed and whispered, "Hand me the lube."

She handed me the lube and sat on the bed. I squeezed out more lube onto my cock and guided her hand to me, letting her spread the lube. Then I squeezed some onto my hand and worked it over her erection, sliding up and down. After I was sure we both were well lubricated I squeezed some more onto my finger and worked it over and then into her ass, working my finger into her.

"Do you want me to turn over?"

"No, I want to watch you, see your face... your cock as we do this."

Gently pushing her back onto the bed, I grabbed her legs and slid her a bit closer and then moved my cock down under hers. Holding it with one hand I guided the head against her asshole and leaned onto her but couldn't work it in.

"I'm sorry, but..."

"Shh, it's okay. Just relax," I said, moving one hand to her cock and stroking it slowly. Noticing her sliding her palms over her nipples I tried again, leaning against her. Slowly she opened to me and I eased into her.

The sensation was intense, so tight that I could feel every movement her body made, every breath she made as her tight opening gripped me. I remained still for a few moments and then slowly backed out a bit and then pushed in further. Watching her face as I moved into her I would slow when I saw her wince and then gently slide further. After a few thrusts I pushed my cock until I met some firm resistance.

"Okay, I think you'll need to try to relax again," I whispered, working her cock some more. When she nodded, I leaned onto her, letting my weight help me press into her.

I heard a slight squeal and then felt her open completely to me. Feeling my cock slid into the hilt I paused again. "Are you okay?"

"It hurt, but seems okay now."

"I'll go slow okay?"

When she nodded I eased my cock out slightly and then pressed back into her. After a few short thrusts I looked at her face and slid back to where I could feel myself being forced out by her muscles and then I pressed back into her.

"Ooo yeah," she moaned, "that was nice."

I continued moving back and then pressing deep into her, feeling her tightness around me. As I moved I reached down wrapped my fingers around my cock. Pressing into her I moved my hand in unison with my motion so when I pushed myself to the hilt my hand reached the base of her cock.

Moving in and out of her I could feel myself getting closer and closer when she suddenly lifted herself up to me and groaned, "I'm coming," spurting her cum up onto her breasts. I paused in my thrusts to feel her ass tighten on me with each spurt. When the spurting subsided, I then concentrated on the tight sensation of her on my cock.

Each thrust enveloped me in pleasure and when she reached up and ran her fingers over my nipples it seemed electric. I eased back and then plunged into her, hearing her whispering, "Come on, give it to me." Hearing her, feeling her, seeing her cum glistening on her breasts was too much. I arched my back and came, shooting my cum deep into her again and again.

Collapsing onto her I quickly rolled onto my side to avoid smothering her. Sadly my cock slipped out of her as I moved. After a few minutes she got up and went into the bathroom, returning with a towel which she used to dab up the cum on her breasts and then cleaned off my cock.

"Wow, I never felt anything like that before," I said, sitting up.

"It was so intense. I mean it hurt, still does a bit, but oh, it was so much more than I thought. By myself It felt good, but nothing... nothing like that."

"So what do we do now?"

"Now?"

"The money."

"Look, I know I wasn't... what if you paid me half?"

"Half?"

"I am half woman now, you pay me half."

"Sounds fair," I nodded standing up and grabbing my phone. Sitting down at the desk I watched as she gathered up her clothes and began to dress. Watching her move, remembering how it felt deep inside her, the excitement I felt as her cum splashed onto her breasts, I sent instructions to release the full payment. "It's done," I said, grabbing my clothes and quickly dressing.

"Thank you," she said, easing her arms through her bra straps, "I'm sorry I wasn't what you..."

Moving over to her I pulled her to me and said, "You were wonderful." Leaning forward I kissed her forehead and then stepped back. As she pulled on her blouse I thought to myself, beautiful, thin but still beautiful.

We rode down in the elevator and I walked her out to the waiting limo. Once inside, she rolled down the window and said, "Thank you again."

"I hope the operation... ah I mean I hope you can pay off your loans okay."

She smiled as the limo pulled away.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
Share this Story

story TAGS

Similar Stories

How I Met Sheri Pt. 01 How a girl found her way into my cold heart. Fiction.in Transgender & Crossdressers
A Big Surprise! A weekend get away to share kinky truths and a big surprise.in Transgender & Crossdressers
Caught Red Handed Pt. 01 Marc gets caught red handed by principal & must get punished.in Transgender & Crossdressers
Quite the Shocker Gurl lusts after her nephew and he takes her.in Transgender & Crossdressers
Do You Think I'm Sexy? A straight man is seduced by his crossdressing roommate.in Transgender & Crossdressers
More Stories